C-H···F interactions in the crystal structures of some fluorobenzenes

Journal of the American Chemical Society

Volumn 120, Issue 34, 1998, Pages 8702-8710

  Thalladi, Venkat R ^a   Weiss, Hans Christoph ^b   Bläser, Dieter ^b   Boese, Roland ^b   Nangia, Ashwini ^a   Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FLUOROBENZENE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 0032475420     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981198e     Document Type: Article

References (72)

1. For selected reviews that describe the use of hydrogen bonding in crystal engineering, see: (a) Subramanian, S.; Zaworotko, M. J. Coord. Chem. Rev. 1994, 137, 357. (b) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397. (c) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, The Netherlands, 1989; pp 115-173.
2. For selected reviews that describe the use of hydrogen bonding in crystal engineering, see: (a) Subramanian, S.; Zaworotko, M. J. Coord. Chem. Rev. 1994, 137, 357. (b) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397. (c) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, The Netherlands, 1989; pp 115-173.
3. For selected reviews that describe the use of hydrogen bonding in crystal engineering, see: (a) Subramanian, S.; Zaworotko, M. J. Coord. Chem. Rev. 1994, 137, 357. (b) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397. (c) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, The Netherlands, 1989; pp 115-173.
4. (a) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154.
5. (b) Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, 1995.
6. (c) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37.
7. (d) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229.
8. Pauling, L. The Nature of the Chemical Bond; Cornell University Press: Ithaca, NY, 1960.
9. Harrell, S. A.; McDaniel, D. H. J. Am. Chem. Soc. 1964, 86, 4497.
10. (a) Murray-Rust, P.; Stallings, W. C.; Monti, C. T.; Preston, R. K.; Glusker, J. P. J. Am. Chem. Soc. 1983, 105, 3206.
11. (b) Shimoni, L.; Carrell, H. L.; Glusker, J. P.; Coombs, M. M. J. Am. Chem. Soc. 1994, 116, 8162.
12. Shimoni, L.; Glusker, J. P. Struct. Chem. 1994, 5, 383.
13. Howard, J. A. K.; Hoy, V. J.; O'Hagan, D.; Smith, G. T. Tetrahedron 1996, 52, 12613.
14. Dunitz, J. D.; Taylor, R. Chem. Eur. J. 1997, 3, 89.
15. For selected reviews that describe the use of weak hydrogen bonding in crystal engineering, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441. (c) Steiner, T. Cryst. Rev. 1996, 6, 1. (d) Desiraju, G. R. Science 1997, 278, 404. (e) Desiraju, G. R. Chem. Commun. 1997, 1475.
16. For selected reviews that describe the use of weak hydrogen bonding in crystal engineering, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441. (c) Steiner, T. Cryst. Rev. 1996, 6, 1. (d) Desiraju, G. R. Science 1997, 278, 404. (e) Desiraju, G. R. Chem. Commun. 1997, 1475.
17. For selected reviews that describe the use of weak hydrogen bonding in crystal engineering, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441. (c) Steiner, T. Cryst. Rev. 1996, 6, 1. (d) Desiraju, G. R. Science 1997, 278, 404. (e) Desiraju, G. R. Chem. Commun. 1997, 1475.
18. For selected reviews that describe the use of weak hydrogen bonding in crystal engineering, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441. (c) Steiner, T. Cryst. Rev. 1996, 6, 1. (d) Desiraju, G. R. Science 1997, 278, 404. (e) Desiraju, G. R. Chem. Commun. 1997, 1475.
19. For selected reviews that describe the use of weak hydrogen bonding in crystal engineering, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441. (c) Steiner, T. Cryst. Rev. 1996, 6, 1. (d) Desiraju, G. R. Science 1997, 278, 404. (e) Desiraju, G. R. Chem. Commun. 1997, 1475.
20. An interesting recent case of a C-H⋯F hydrogen bond arising from enhanced C-H acidity is provided by 4-ethynylfluorobenzene. See: Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403.
21. (a) Evans, T. A.; Seddon, K. R. Chem. Commun. 1997, 2023.
22. (b) O'Hagan, D.; Rzepa, H. S. Chem. Commun. 1997, 645 and references therein.
23. (c) Glusker, J. P. Acta Crystallogr. 1995, D51, 418.
24. (a) Desiraju, G. R.; Parthasarathy, R. J. Am. Chem. Soc. 1989, 111, 8725.
25. (b) Fernández-Castaño, C.; Foces-Foces, C.; Cano, F. H.; Claramunt, R. M.; Escolático, C.; Fruchier, A.; Elguero, J. New. J. Chem. 1997, 21, 195.
26. Brock, C. P.; Kuo, M.; Levy, H. A. Acta Crystallogr. 1978, B34, 981.
27. Nussbaumer, M.; Boese, R. In Correlations, Transformations, and Interactions in Organic Crystal Chemistry, IUCr Crystallographic Symposia, Vol. 7; Jones, D. W., Katrusiak, A., Eds.; Oxford University Press: Oxford, 1994; pp 20-37.
28. (a) Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
29. (b) Sheldrick, G. M. SHELXL-93 Program for the Refinement of Crystal Structures; University of Göttingen, Germany.
30. Allen, F. H.; Davies, J. E.; Galloy, J. J.; Johnson, O.; Kennard, O.; Macrae, C. F.; Mitchell, E. M.; Mitchell, G. F.; Smith, J. M.; Watson, D. G. J. Chem. Inf. Comput. Sci. 1991, 31, 187.
31. (a) Swift, J. A.; Pal, R.; McBride, J. M. J. Am. Chem. Soc. 1998, 120, 96.
32. (b) Helmle, O.; Csöregh, I.; Weber, E.; Hens, T. J. Phys. Org. Chem. 1997, 10, 76.
33. (c) Fei, X.; Hui, Y.-Z.; Rüdiger, V.; Schneider, H.-J. J. Phys. Org. Chem. 1997, 10, 305.
34. (d) Corey, E. J.; Rohde, J. J.; Fischer, A.; Azimioara, M. D. J. Am. Chem. Soc. 1997, 38, 333.
35. (e) Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018.
36. (f) Kumar, V. A.; Begum, N. S.; Venkatesan, K. J. Chem. Soc., Perkin. Trans. 2 1993, 463.
37. (g) Kumar, V. A.; Venkatesan, K. J. Chem. Soc., Perkin. Trans. 2 1993, 2429.
38. (h) Williams, J. F.; Cockcroft, J. K.; Fitch, A. N. Angew. Chem., Int. Ed. Engl. 1992, 31, 1655.
39. Such a comparison, in which the donor is always the same whereas the acceptor groups (O, N, and F) are varied, is expected to be important in validating the acceptor properties of the C-F group.
40. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
41. (a) Madhavi, N. N. L.; Katz, A. K.; Carrell, H. L.; Nangia, A.; Desiraju, G. R. Chem. Commun. 1997, 1953.
42. (b) Weiss, H.-C; Bläser, D.; Boese, R.; Doughan, B. M.; Haley, M. M. Chem. Commun. 1997, 1703.
43. Boenigk, D.; Mootz, D. J. Am. Chem. Soc. 1988, 110, 2135.
44. 1, we found that it can be represented better in the tetragonal system.
45. Fauvet, G.; Massaux, M.; Chevalier, R. Acta Crystallogr. 1978, B34, 1376.
46. (a) Grepioni, F.; Cojazzi, G.; Draper, S. M.; Scully, N.; Braga, D. Organometallics 1998, 17, 296.
47. (b) Ashton, P. R.; Fyfe, M. C. T.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 12514.
48. (c) Kiplinger, J. L.; Arif, A. M.; Richmond, T. G. Inorg. Chem. 1995, 34, 399.
49. (d) Kiplinger, J. L.; Richmond, T. G.; Arif, A. M.; Dücker-Benfer, C.; van Eldik, R. Organometallics 1996, 15, 1545.
50. (a) Thalladi, V. R.; Panneerselvam, K.; Carrell, C. J.; Carrell, H. L.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1995, 341.
51. (b) Reddy, D. S.; Goud, B. S.; Panneerselvam, K.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 663.
52. (c) Thalladi, V. R.; Brasselet, S.; Bläser, D.; Zyss, J.; Boese, R.; Nangia, A.; Desiraju, G. R. Chem. Commun. 1997, 1841.
53. Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thalladi, V. R.; Desiraju, G. R.; Wilson, C. C.; McIntyre, G. J. J. Am. Chem. Soc. 1997, 119, 3477.
54. Trotter, J. Acta Crystallogr. 1960, 13, 86.
55. Britton, D. Acta Crystallogr. 1976, B32, 976.
56. 2 ≈ 90°, the contact is defined as type II. See: Ramasubbu, N.; Parthasarathy, R.; Murray-Rust, P. J. Am. Chem. Soc. 1986, 108, 4308.
57. 1 (No. 4), a = 4.2000(8), b = 5.6800(11), and c = 13.590(3) Å, β = 98.67(3)°, Z= 2, T = 120 K.
58. We are stating here that even when a short type-I F⋯F geometry is seen, it is only as a result of close-packing or it may even be repulsive. Such a conclusion is further strengthened by the fact that type-II F⋯F contacts are rarely seen, if at all (see: Thalladi, V. R.; Weiss, H.-C; Boese, R.; Nangia, A.; Desiraju, G. R. To be submitted).
59. The other sym-trihalobenzenes are isostructural but quite different from 7. These structures are fully stabilized by type-II X⋯X interactions showing again the distinctive behaviour of F vis-à-vis the heavier halogens. (a) For 1,3,5-trichlorobenzene and 1,3,5-tribromobenzene, see: Milledge, H. J.; Pant, L. M. Acta Crystallogr. 1960, 13, 285.
60. (b) For 1,3,5-triiodobenzene, see: Thalladi, V. R.; Hoy, V. J.; Howard, J. A. K.; Allen, F. H.; Desiraju, G. R. Unpublished results.
61. Coppens, P. Science 1967, 158, 1577.
62. Bernstein, J.; Cohen, M. D.; Leiserowitz, L. In The Chemistry of Quinonoid Compounds; Patai, S., Ed.; Interscience: New York, 1974; p 37.
63. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555.
64. It is interesting to note that the tetramer synthon III is also observed in the structure of 3, a molecule that contains the complementary number and location of hydrogen-bond donors and acceptors.
65. Bertinotti, F.; Giacomello, G.; Liquori, A. M. Acta Crystallogr. 1956, 9, 510.
66. Unsurprisingly, these structures do not resemble those of 1,2,4,5-tetrachloro-or -tetrabromobenzene.
67. Kottke, T.; Sung, K.; Lagow, R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1517.
68. Note that such packing is similar to that observed in the crystal structure of pyrene. See: Desiraju, G. R.; Gavezzotti, A. J. Chem. Soc., Chem. Commun. 1989, 621.
69. 2 Program, Molecular Simulations, 9685 Scranton Road, San Diego, CA 92121-3752, and 240/250 The Quorum, Barnwell Road, Cambridge CB5 8RE, UK.
70. (b) For a description of the polymorph prediction sequence used by the program, see: Gdanitz, R. J. In Theoretical Aspects and Computer Modeling of the Molecular Solid State; Gavezzotti, A., Ed.; Wiley: Chichester, 1997; pp 185-202.
71. Molecular minimizations were performed with the AM1 Hamiltonian in Mopac 6.0 and ESP charges were assigned. The Dreiding 2.21 force field was used for all calculations involved in the prediction. The prediction sequence was repeated twice to check its reproducibility.
72. 1/n reproduced the diads and the general sandwich herringbone packing as seen in 9b.